3-methoxy-1,4-diphenylazetidin-2-one | 33812-89-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 3-methoxy-1,4-diphenylazetidin-2-one
• 英文别名: (3S,4R)-3-methoxy-1,4-diphenylazetidin-2-one
• CAS: 33812-89-4
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: ANULBTRTUMKSEO-CABCVRRESA-N

物化性质

• 熔点：
  138-140 °C(Solv: hexane (110-54-3); ethanol (64-17-5))
• 沸点：
  461.5±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-苄叉苯胺 、 甲氧基乙酸 在 三乙胺 、 对甲苯磺酰氯 作用下， 以 苯 为溶剂， 反应 2.0h， 以52%的产率得到3-methoxy-1,4-diphenylazetidin-2-one
  参考文献：
  名称：

  Cycloadditions of (alkylarylamino)ketenes with imines. cis-3-Amino-2-azetidinones

  摘要：

  DOI：

  10.1021/jo00273a012

文献信息

• Syntheses of β-lactams from acetic acids and imines induced by phenyl dichlorophosphate reagent
  作者：Ana Arrieta、Fernando P. Cossio、Claudio Palomo

  DOI：10.1016/s0040-4020(01)96484-1

  日期：——

  Among the reagents known to produce β-lactams from imines and acetic acids, only phenyl dichlorophosphate and 1-methyl-2-chloropyridinium iodide are suitable for the synthesis of vinylamino- β-lactams. Reaction of acetic acids with ethanolimine derivatives promoted by phenyl dichlorophosphate affords oxazolidines instead β-lactams. Protection of the hydroxyl group as the trimethylsilyl ether in the

  描述了从丹尼盐和席夫碱制备乙烯基氨基-β-内酰胺的实用方法的开发。在已知可从亚胺和乙酸生产β-内酰胺的试剂中，只有苯基二氯磷酸酯和1-甲基-2-氯吡啶碘代碘适合用于合成乙烯基氨基-β-内酰胺。乙酸与由二氯磷酸苯酯促进的乙醇亚胺衍生物反应生成恶唑烷，而不是β-内酰胺。在起始席夫碱中保护羟基作为三甲基甲硅烷基醚提供了通往相应的β-内酰胺而不是恶唑烷的便利途径。对该方法的范围进行了一些观察。
• Triphenylphosphine dibromide and dimethylsulfide dibromide as versatile reagents for beta-lactam synthesis
  作者：Fernando P. Cossío、Iñaki Ganboa、Claudio Palomo

  DOI：10.1016/s0040-4039(00)98613-1

  日期：1985.1

  Triphenylphosphine dibromide and dimethylsulfide dibromide are efficient reagents for the direct synthesis of beta-lactams from carboxylic acids and imines avoiding the use of acid halides as starting materials. Synthesis of 4-imino-beta-lactams are also briefly described. A potential synthesis of N-unsubstituted beta-lactams is made.

  三苯基膦二溴化物和二甲基硫醚二溴化物是从羧酸和亚胺直接合成β-内酰胺的有效试剂，避免了使用酰卤作为原料。还简要描述了4-亚氨基-β-内酰胺的合成。制备了N-未取代的β-内酰胺的潜在合成物。
• Synthesis of 3-acetoxyazetidin-2-ones and 3-hydroxyazetidin-2-ones with antifungal and antibacterial activity
  作者：OM Walsh、MJ Meegan、RM Prendergast、T Al Nakib

  DOI：10.1016/s0223-5234(97)86178-8

  日期：1996.1

  The synthesis of a series of 3-acetoxyazetidin-2-ones 3a-n and 3-hydroxyazetidin-2-ones 6a-j is reported together with the antibacterial and antifungal evaluation of these compounds. An additional series of 3-acetoxyazetidin-2-ones 11a-h which possess a free carboxylic acid group on the N-1 aryl ring were obtained by treatment of suitably substituted Schiff bases 10a-h with acetoxyacetyl chloride. The novel bicyclic structures 7 acetoxy-6-phenyl-5-thia-1-azabicyclo[4.2.0]octan-8-one 13 and 7-hydroxy-6-phenyl-5-thia-1-azabicyclo[4.2.0]octan-8-one 14 were also obtained. Many of the compounds displayed antifungal activity in vitro when evaluated against the pathogenic fungi Cryptococcus neoformans, Candida albicans, Candida tropicalis, Candida parapsilosis, Candida glabrata, and Trichosporon cutaneum, while 3-acetoxyazetidin-2-ones 11a-h containing a free carboxylic acid group on the N-1 aryl ring displayed antibacterial activity against Staphylococcus aureus, Proteus vulgaris, Pseudomonas aeruginosa, Bacillus subtilis, Klebsiella aerogenes and Escherischia coli.
• A Convenient Synthesis of β-Lactams
  作者：Muneharu Miyake、Makoto Kirisawa、Norio Tokutake

  DOI：10.1055/s-1982-30061

  日期：——
• Yadav, Ram Naresh; Chavez, Ashlee; Banik, Bimal Krishna, Journal of the Indian Chemical Society, 2018, vol. 95, # 11, p. 1365 - 1367
  作者：Yadav, Ram Naresh、Chavez, Ashlee、Banik, Bimal Krishna

  DOI：——

  日期：——